Should we go after Venture Capital, and when?

You need it. If the only way you can get to the next level is to raise capital, then do it. I needed to for both my start-ups, up to a point, for different reasons.

or

It’s “cheap”. Venture capital is very expensive in the early days, in terms of dilution. But later, it gets pretty cheap. It can either be cheap in that the ROI is high — e.g., you make $5 back for every $1 you invest. That usually is incredibly accretive for your founders’ stock. This is the ideal reason to raise a Series “B” or “C” round. And in later stages, if you can raise money at huge valuations, the rounds literally can be very cheap in terms of dilution % for $ raised. Airbnb will never even notice the dilution from its last rounds, to take an extreme example. In either or both cases, venture capital can be a great deal.

The trap is raising in other scenarios. Founders often raise venture capital because they can … but they don’t need to, and it’s not cheap / very high ROI.

If you do that and it’s just one round, no big deal. If you do that over multiple rounds, before the capital is “cheap” … you’ll end up diluted far more than you realize. And possibly losing more control than was really necessary.